Prooxidant activity of hydroxycinnamic acids on DNA damage in the presence of Cu(II) ions: Mechanism and structure-activity relationship

Food and Chemical Toxicology

Volumn 46, Issue 1, 2008, Pages 149-156

  Zheng, Li Fang ^a   Dai, Fang ^a   Zhou, Bo ^a   Yang, Li ^a   Liu, Zhong Li ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Caffeic acid; Copper; DNA damage; Hydroxycinnamate; Reactive oxygen species; Structure activity relationship

Indexed keywords

CAFFEIC ACID; CHLOROGENIC ACID; COUMARIC ACID; CUPRIC ION; FERULIC ACID; META COUMARIC ACID; PARA COUMARIC ACID; SINAPIC ACID; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; DNA DAMAGE; ELECTRON TRANSPORT; GEL ELECTROPHORESIS; NONHUMAN; STRUCTURE ACTIVITY RELATION; ULTRAVIOLET SPECTROSCOPY;

ANIMALS; CATTLE; COPPER; COUMARIC ACIDS; DNA DAMAGE; OXIDANTS; OXIDATIVE STRESS; SPECTROPHOTOMETRY, ULTRAVIOLET; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 36849028123     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2007.07.010     Document Type: Article

References (44)

1. Ahmad A., Asad S.F., Singh S., and Hadi S.M. DNA breakage by resveratrol and Cu(II): reaction mechanism and bacteriophage inactivation. Cancer Lett. 154 (2000) 29-37
2. Ahsan H., and Hadi S.M. Strand scission in DNA induced by curcumin in the presence of Cu(II). Cancer Lett. 124 (1998) 23-30
3. Aruoma O.I., Halliwell B., Gajewski E., and Dizdaroglu M. Copper-ion dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochem. J. 273 (1991) 601-604
4. Azmi A.S., Bhat S.H., and Hadi S.M. Resveratrol-Cu(II) induced DNA breakage in human peripheral lymphocytes: implications for anticancer properties. FEBS Lett. 579 (2005) 3131-3135
5. Azmi A.S., Bhat S.H., Hanif S., and Hadi S.M. Plant polyphenols mobilize endogeneous copper in human peripheral lymphocytes leading to oxidative DNA breakage: a putative mechanism for anticancer properties. FEBS Lett. 580 (2006) 533-538
6. Briante R., Febbraio F., and Nucci R. Antioxidant properties of low molecular weight phenols present in the mediterranean diet. J. Agric. Food Chem. 51 (2003) 6975-6981
7. Bowry V.W., and Ingold K.U. The unexpected role of vitamin E (α-tocopherol) in the peroxidation of human low-density lipoprotein. Acc. Chem. Res. 32 (1999) 27-34
8. Bowry V.W., and Stocker R. Tocopherol-mediated peroxidation. The prooxidation effect of vitamin E on the radical-initiated oxidation of human low-density lipoprotein. J. Am. Chem. Soc. 115 (1993) 6029-6044
9. Buettner G.R. Ascorbate autoxidation in the presence of ion and copper chelates. Free Radic. Res. Commun. 1 (1986) 349-353
10. Cai L., Tsiapalis G., and Cherian M.G. Protective role of zinc-metallothionein on DNA damage in vitro by ferric nitrilotriacetate (Fe-NTA) and ferric salts. Chem. Biol. Interact. 115 (1998) 141-151
11. Chen W.-F., Deng S.-L., Zhou B., Yang L., and Liu Z.-L. Curcumin and its analogues as potent inhibitors of low density lipoprotein oxidation: H-atom abstraction from the phenolic groups and possible involvement of the 4-hydroxy-3-methoxyphenyl groups. Free Radic. Biol. Med. 40 (2006) 526-535
12. Cheng J.-C., Dai F., Zhou B., Yang L., and Liu Z.-L. Antioxidant activity of hydroxycinnamic acid derivatives in human low density lipoprotein: mechanism and structure-activity relationship. Food Chem. 104 (2007) 132-139
13. Cheng J.-C., Fang J.-C., Chen W.-F., Zhou B., Yang L., and Liu Z.-L. Structure-activity relationship studies of resveratrol and its analogues by the reaction kinetics of low density lipoprotein peroxidation. Bioorg. Chem. 34 (2006) 142-157
14. Dai F., Miao Q., Zhou B., Yang L., and Liu Z.-L. Protective effects of flavonols and their glycosides against free radical-induced oxidative hemolysis of red blood cells. Life Sci. 78 (2006) 2488-2493
15. Foti M., and Ruberto G. Kinetic solvent effects on phenolic antioxidant determined by spectrophotometric measurements. J. Agric. Food Chem. 49 (2001) 342-348
16. Fukuhara K., and Miyata N. Resveratrol as a new type of DNA-cleaving agent. Bioorg. Med. Chem. Lett. 8 (1998) 3187-3192
17. Fukuhara K., Nagakawa M., Nakanishi I., Ohkubo K., Imai K., Urano S., Fukuzumi S., Ozawa T., Ikota N., Mochizuki M., Miyata N., and Okuda H. Structural basis for DNA-cleaving activity of resveratrol in the presence of Cu(II). Bioorg. Med. Chem. 14 (2006) 1437-1443
18. Galati G., and O'Brien P.J. Potential toxicity of flavonoids and other dietary phenolics: significance for their chemopreventive and anticancer properties. Free Radic. Biol. Med. 37 (2004) 287-303
19. Hadi S.M., Asad S.F., Singh S., and Ahmad A. Putative mechanism for anticancer and apoptosis-inducing properties of plant-derived polyphenolic compounds. IUBMB Life 50 (2000) 167-171
20. Haque M.E., Asanuma M., Higashi Y., Miyazaki I., Tanaka K.I., and Ogawa N. Apoptosis-inducing neurotoxicity of dopamine and its metabolites via reactive quinone generation in neuroblastoma cells. Biochim. Biophys. Acta 1619 (2003) 39-52
21. Hayakawa F., Kimura T., Maeda T., Fujita M., Sohmiya H., Fujii M., and Ando T. DNA cleavage reaction and linoleic acid peroxidation induced by tea catechins in the presence of cupric ion. Biochim. Biophys. Acta 1336 (1997) 123-131
22. Hider B.C., Liu Z.D., and Khodr H.H. Metal chelation of polyphenols. Meth. Enzymol. 335 (2001) 190-203
23. Hotta H., Nagano S., Ueda M., Tsujino Y., Koyama J., and Osakai T. Higher radical scavenging activities of polyphenolic antioxidants can be ascribed to chemical reactions following their oxidation. Biochim. Biophys. Acta 1572 (2002) 123-132
24. Jung Y.-J., and Surh Y.-J. Oxidative DNA damage and cytotoxicity induced by copper-stimulated redox cycling of salsolinol, a neurotoxic tetrahydroisoquinoline alkaloid. Free Radic. Biol. Med. 30 (2001) 1407-1417
25. Laranjinha J., Vieira O., Madeira V., and Almeida L. Two related phenolic antioxidants with opposite effects on vitamin E content in low density lipoprotein oxidized by ferrylmyoglobin: consumption vs regeneration. Arch. Biochem. Biophys. 323 (1995) 373-381
26. Li A.H., Bandy B., Tsang S.S., and Davison A. DNA-breaking versus DNA-protecting activity of four phenolic compounds in vitro. Free Radic. Res. 33 (2000) 551-566
27. Milne L., Nicotera P., Orrenius S., and Burkitt M.J. Effects of Glutathione and chelating agents on copper-mediated DNA oxidation: pro-oxidant and antioxidant properties of glutathione. Arch. Biochem. Biophys. 304 (1993) 102-109
28. Nardini M., D'Aquino M., Tomassi G., Gentili V., Di Felice M., and Scaccini C. Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Radic. Biol. Med. 19 (1995) 541-552
29. Patel K.B., and Wilson R.L. Semiquinone free radicals and oxygen. Pulse radiolysis study of one electron transfer equilibria. J. Chem. Soc. Faraday Trans. 69 (1973) 814-825
30. Podmore I.D., Griffiths H.R., Herbert K.E., Mistry N., Mistry P., and Lunec J. Vitamin C exhibits pro-oxidant properties. Nature 392 (1998) 559
31. Radtke J., Linseisen J., and Wolfram G. Phenolic acid intake of adults in Bavarian subgroup of the national food consumption survey. Zeitschrift für Ernahrungswissenschaft 37 (1998) 190-197
32. Robbins R.J. Phenolic acids in foods: an overview of analytical methodology. J. Agric. Food Chem. 51 (2003) 2866-2887
33. Roche M., Dufour C., Mora N., and Dangles O. Antioxidant activity of olive phenols: mechanistic investigation and characterization of oxidation products by mass spectrometry. Org. Biomol. Chem. 3 (2005) 423-430
34. Sakihama Y., Cohen M.F., Grace S.C., and Yamasaki H. Plant phenolic antioxidant and prooxidant activities: phenolics-induced oxidative damage mediated by metals in plants. Toxicology 177 (2002) 67-80
35. Samuni A.M., Chuang E.Y., Krishna M.C., Stein W., DeGraff W., Russo A., and Mitchell J.B. Semiquinone radical intermediate in catecholic estrogen-mediated cytotoxic and mutagenesis: chemoprevention strategies with antioxidants. Proc. Natl. Acad. Sci. USA 100 (2003) 5390-5395
36. Schweigert N., Hunziker R., Escher B.J., and Eggen R.I.L. The acute toxicity of (chloro-) catechol and (chloro-catechol/copper combinations in Escherichia coil corresponds to the membrane toxicity of these compounds. Environ. Toxicol. Chem. 20 (2001) 239-247
37. Silva F.A.M., Borges F., Guimarães C., Lima J.L.F.C., Matos C., and Reis S. Phenolic acid and derivatives: Studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J. Agric. Food Chem. 48 (2000) 2122-2126
38. Stoewe R., and Prutz W.A. Copper-catalyzed DNA damage by ascorbate and hydrogen peroxide: kinetics and yield. Free Radic. Biol. Med. 3 (1987) 97-105
39. Taubert D., Breitenbach T., Lazar A., Censarek P., Harlfinger S., Berkels R., Klaus W., and Roesen R. Reaction rate constants of superoxide scavenging by plant antioxidants. Free Radic. Biol. Med. 35 (2003) 1599-1607
40. Wright J.S., Johnson E.R., and Dilabio G.A. Predicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidant. J. Am. Chem. Soc. 123 (2001) 1173-1183
41. 2+-induced low density lipoprotein oxidation. FEBS Lett. 405 (1997) 186-190
42. Yamashita N., Murata M., Inoue S., BurKitt M.J., Miline L., and Kawanishi S. α-Tocopherol induces oxidative damage to DNA in the presence of copper(II) ions. Chem. Res. Toxicol. 11 (1998) 855-862
43. Yamashita N., Tanemura H., and Kawanishi S. Mechanism of oxidative DNA damage induced by quercetin in the presence of Cu(II). Mutat. Res. 425 (1999) 107-115
44. Zhou B., Miao Q., Yang L., and Liu Z.-L. Antioxidative effects of flavonols and their glycosides against the free-radical-induced peroxidation of linoleic acid in solution and in micelles. Chem. Eur. J. 11 (2005) 680-691